The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Interior Surface Modification of Bacteriophage MS2
Abstract
An efficient strategy for the interior surface functionalization of MS2 viral capsids is reported, featuring a new hetero-Diels-Alder bioconjugation reaction. After virus isolation, the RNA genome was removed from the spherical particles by exposure to pH 11.8 conditions for a period of 4 h. Following this, 180 tyrosine residues on the interior surface of each "empty" capsid shell were modified by using a site-selective diazonium-coupling reaction. To attach additional functionality, the azo conjugate was reduced with Na2S2O4 to afford an ortho-amino tyrosine derivative. Oxidation of this moiety with NaIO4 produced an o-iminoquinone on the protein surface, which was found to undergo an efficient hetero-Diels-Alder reaction with N-(4-aminophenyl)acrylamide. This four-step procedure can be carried out in under 4 h, reaches high levels of conversion, and yields the desired conjugates in >60% overall yield.
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Cites
The three-dimensional structure of the bacterial virus MS2
Valegård, K., Liljas, L., Fridborg, K., & Unge, T. (1990) · Nature · doi:10.1038/345036a0 · Cited by 411
Cited by
Yi, H., Wu, L.-Q., Bentley, W. E., Ghodssi, R., Rubloff, G. W., Culver, J. N., & Payne, G. F. (2005) · Biomacromolecules · doi:10.1021/bm050410l · Cited by 759
Algar, W. R., Prasuhn, D. E., Stewart, M. H., Jennings, T. L., Blanco-Canosa, J. B., Dawson, P. E., & Medintz, I. L. (2011) · Bioconjugate Chemistry · doi:10.1021/bc200065z · Cited by 502
Virus-based nanocarriers for drug delivery
Ma, Y., Nolte, R. J. M., & Cornelissen, J. J. L. M. (2012) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2012.01.005 · Cited by 422
Cell-Specific Delivery of Diverse Cargos by Bacteriophage MS2 Virus-like Particles
Ashley, C. E., Carnes, E. C., Phillips, G. K., Durfee, P. N., Buley, M. D., Lino, C. A., Padilla, D. P., Phillips, B., Carter, M. B., Willman, C. L., et al. (2011) · ACS Nano · doi:10.1021/nn201397z · Cited by 350
Tamura, T., & Hamachi, I. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b11747 · Cited by 339
Metadata
- Authors
- Hooker, J. M., Kovacs, E. W., & Francis, M. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-03-01
- Volume
- 126
- Issue
- 12
- Pages
- 3718-3719
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2025747013
- Cited by
- 334
- References
- 1
- FWCI
- 16.69
- Type
- journal article
- Language
- en
- Open access
- closed
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- Hooker, J. M., Kovacs, E. W., & Francis, M. B. (2004). Interior Surface Modification of Bacteriophage MS2. Journal of the American Chemical Society. https://doi.org/10.1021/ja031790q
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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